4-(2-{[(2S)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol

• ChemBase ID: 120171
• Molecular Formular: C18H23NO3
• Molecular Mass: 301.38012
• Monoisotopic Mass: 301.1677936
• SMILES: c1(c(ccc(c1)CCN[C@@H](CCc1ccc(cc1)O)C)O)O
• Canonical SMILES: C[C@H](CCc1ccc(cc1)O)NCCc1ccc(c(c1)O)O
• InChI: InChI=1S/C18H23NO3/c1-13(2-3-14-4-7-16(20)8-5-14)19-11-10-15-6-9-17(21)18(22)12-15/h4-9,12-13,19-22H,2-3,10-11H2,1H3
• InChIKey: JRWZLRBJNMZMFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{[(2S)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
• IUPAC Traditional name: 4-(2-{[(2S)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol; (S)-dobutamine
• Synonyms: Dobutrex; Inofrex; Dobutamine hydrochloride; (S)-4-(2-((4-(4-hydroxyphenyl)butan-2-yl)amino)ethyl)benzene-1,2-diol

Database IDs

• CAS Number: 52663-81-7
• PubChem SID: 162214524
• PubChem CID: 688441

CALCULATED PROPERTIES

• Acid pKa: 10.141794
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.55885684
• LogD (pH = 7.4): 1.1584939
• Log P: 2.6162553
• Molar Refractivity: 88.3911 cm^3
• Polarizability: 34.158314 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Stimulation of beta1 receptors of the sympathetic nervous system

Product Information

• Application(s): Sympathomimetic drug; Used in the treatment of heart failure and cardiogenic shock

REFERENCES

• Tuttle RR, Mills J (January 1975). "Dobutamine: development of a new catecholamine to selectively increase cardiac contractility". Circ Res 36 (1): 185?6. PMID 234805.
• Rang HP, Dale MM, Ritter JM, Flower RJ. Rang and Dale's Pharmacology.
• Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 6. ISBN 1-59541-101-1.
• Parker K, Brunton L, Goodman LS, Blumenthal D, Buxton I (2008). Goodman & Gilman's manual of pharmacology and therapeutics. McGraw-Hill Medical. pp. 159. ISBN 0-07-144343-6.
• Tibayan FA, Chesnutt AN, Folkesson HG, Eandi J, Matthay MA (1997). "Dobutamine increases alveolar liquid clearance in ventilated rats by beta-2 receptor stimulation".
• Am. J. Respir. Crit. Care Med. 156 (2 Pt 1): 438?4. PMID 9279221